Characteristic properties of cutting fluid additives derived from the derivatives of ricinoleic acid polymers

A number of esters were prepared from the reaction of acid chlorides with ricinoleic acid polymers and screened for anti-rust properties and antimicrobial activity in spent coolants of water-based cutting fluids. Aqueous solutions of triethanolamine salts with decanoic acid, undecanoic acid and oleic acid esters of ricinoleic acid dimer, trimer, tetramer and hexamer showed good anti-rust properties for water-based cutting fluids. Dehydrates of ricinoleic acid polymers also showed good anti-rust properties for water-based cutting fluids.     

Characteristic properties of cutting fluid additives derived from half esters of dimer acids

A number of half esters were prepared from the reaction of alcohols with dimer acids and screened for anti-rust properties and antimicrobial activity in spent coolants of water-based cutting fluids. Aqueous solutions of triethanolamine salts with lower-alcohol half esters of dimer acid showed good anti-rust properties for water-based cutting fluids.     

Characteristic properties of cutting fluid additives made from the derivatives of some polymeric nonionic surface-active agents

A series of esters was prepared from the reaction of acid chlorides with polymeric nonionic surface-active agents (copolymer of propylene oxide and ethylene oxide), and they were screened for antirust and other properties associated with water-based cutting fluids. An aqueous emulsion of an adduct of triethanolamine and the oleic acid ester of polymeric nonionic surface-active agent showed excellent antirust properties when used as a water-based cutting fluid. The emulsion of triethanolamine and the mono nonyl ether of the surface-active agent also showed antirust properties.     

Adducts of cyclic acid anhydrides and fatty amines as anti-rust additives in water-based cutting fluids

A variety ofN-alkyl carboxylic acid amides was prepared from the reaction of cyclic dicarboxylic acid anhydrides and various amines, and screened for anti-rust properties and antimicrobial activity in spent coolants of water-based cutting fluids. The triethanol amine salts of the adducts of maleic anhydride with octylamine, decylamine, dodecylamine and oleylamine, and the one of phthalic anhydride with octylamine showed both good anti-rust and antimicrobial activity.     

New additives derived from fatty acids for water-based cutting fluids

A variety of derivatives from long chain fatty acids were prepared, and corrosion and lubricity tests for these products as water-based cutting fluid additives were carried out. We have found that triethanolamine salts of 11-(carboxymethylthio)-undecanoic acid (II), 10,11-dichloromethylene undecanoic acid (IV) and 12-isovaleroyloxy stearic acid (VI) showed effective rust-inhibiting and anti-wear properties for water-based cutting fluids.     

Preparation and surface- active properties of polyoxyethylene-glycol (600) monoesters of fatty acids

Polyoxyethyleneglycol (PEG-600) monoesters of undecylenic, lauric, myristic, palmitic, stearic, oleic, ricinoleic and 12-hydroxystearic acids were prepared in 80-85% yield by reacting PEG with boric acid, esterifying the resultant borate with fatty acid, and selectively hydrolyzing the borate ester; their surface active properties were evaluated. Increase in acyl chain length increased the surface tension. The presence of a double bond or hydroxyl group in C₁₈ series improved the wetting and emulsifying proper-ties. Unsaturation in the fatty acid chain reduced the foaming power.     

Half esters of dibasic acids as additives in water-based cutting fluids

Several half esters from long chain dibasic acids were prepared, and corrosion and lubricity tests for these products as water-based cutting fluid additives were made. Triethanolamine salts of half esters of sebacic acid and dodecanedioic acid showed effective rust-inhibiting and anti-wear properties for water-based cutting fluids.     

Products from the reaction of fatty acids with ketones and their characteristic properties as cutting fluids additives

Hydroxy acids were synthesized in good yields from ketones and fatty acids by the use of lithium naphthalene in the presence of diethylamine. For example, from cyclohexanone and undecylenic acid (I), 2-(1-hydroxy-1-cyclohexyl)-10-undecenoic acid (III) was obtained in 92% yield. Hydroxy acids were treated withp-toluenesulphonic acid to give corresponding unsaturated fatty acids. From the reaction of (III), 2-(1-cyclohexenyl)-10-undecenoic acid (IV), a 3,4-unsaturated acid was obtained (yield 59%). Corrosion and lubricity tests for these products as water-based cutting fluid additives were carried out. We have found that triethanolamine salts of 2-cyclohexenyl and 2-hydroxycyclohexyl fatty acids showed effective rust-inhibiting and antiwear properties for water-based cutting fluids.     

Diels-alder adducts from safflower oil fatty acids: I. Maleic anhydride as dienophile

The Diels-Alder reaction between alkali conjugated and elaidinized safflower oil fatty acids and maleic anhydride was studied under various experimental conditions. The principal product which was obtained in 51–55% yields was a mixture of the adduct of maleic anhydride and maleic acid in 40∶60 proportions. The isolation and properties of this mixed adducts from the reaction mixture and their conversion to trimethyl, tributyl and triallyl esters are described. The trimethyl ester was also obtained in good yield from the methyl esters of the fatty acids and dimethyl maleate.     

DC-Trennung von Ricinusölfettsäure-Estoliden

TLC Separation of Estolides of Castor Oil Fatty Acids Estolides of castor oil fatty acids (polyricinoleic acids) with varying degrees of condensation were synthesized by heating the castor oil fatty acids at 120° C–240° C under vacuum and CO₂ circulation. These products were analyzed by chemical constants and fractionated by TLC on silicagel 60 precoated plates into ricinoleic acid and di-, tri- as well as tetra-ricinoleic acids. Furthermore, the estolides were separated by two-dimensional TLC into two series of estolides, i.e. estolides containing only ricinoleic acid and those which contain fatty acids other than ricinoleic acid at the chain terminal. Hydrogenated castor oil fatty acids (technical 12-hydroxystearic acid) also form estolides which can be fractionated in a similar manner. Thus, TLC provides information on the oligomeric and polymeric character of the estolides of castor oil fatty acids and permits separation even of the decamers.     

以酯基为连接基的非离子双子表面活性剂的合成

以蓖麻油酸（RA）、聚乙二醇（600）为原料,马来酸酐为连接基,合成了一种新型的非离子双子表面活性剂MARAPEG-15,考察了催化剂用量、物料摩尔配比、反应时间及温度对酸酐与蓖麻油酸聚乙二醇硼酸酯酯化的影响,并测定了产物的临界胶束浓度和表面张力。马来酸酐与蓖麻油酸聚乙二醇硼酸酯酯化较佳的工艺条件为：催化剂用量为总质量的3%,n（酸酐）∶n（蓖麻油酸聚乙二醇硼酸酯）为3.1∶2,反应温度为110℃,时间为4 h;硼酸酯键水解时间为1.5 h。产物的表面张力及其临界胶束浓度为γCMC=35.73 mN/m,CMC=1.96×10-5mol/L。     

Water-soluble metal working fluids additives derived from the esters of acid anhydrides with higher alcohols for aluminum alloy materials

Water-soluble metal working fluids are used for processing of aluminum alloy materials. This short article describes properties of new additives in water-soluble metal working fluids for aluminum alloy materials. Many half esters or diesters were prepared from the reactions of higher alcohols with acid anhydrides. Interestingly, diesters of PTMG (tetrahydrofuran oligomer, MW = 650 and 1000) and polybutylene oxide (MW = 650) with maleic anhydride and succinic anhydride showed both of an excellent anti-corrosion property for aluminum alloy and a good hard water tolerance. The industrial soluble type processing oils including these additives also showed anti-corrosion property and hard water tolerance.     

Fat-based dibasic acids

Aside from “dimer acids” (E.C. Leonard’s paper), the best known fat-based dibasic acids consist of eight product types of which only four are commercially important. These are described in detail in this paper: (a.) Azelaic acid produced from oleic acid by either chrome oxidation or ozonolysis of oleic acid also, “brassylic” acid from mixed 55% erucic-containing crambe oil fatty acids. (b). Sebacic acid from castor oil or possibly dodecanedioic acid from lesquerolic acid by caustic fusion. (c) C-21 Dibasic acid by Diels Alder reaction between isomerized TOFA and acrylic acid. (d.) C-19 Dibasic acids (carboxystearic acids) from oleic acid by carboxylation. (e.) Mixed C-11/C-12 Dibasic acids by several routes. Both the alkali cleavage and gentle nitric acid oxidations of certain hydroxy fatty acids (e.g., 12-hydroxystearic acid from hydrogenation of ricinoleic acid, etc.) can be used to afford mixed C-11/C-12 dibasic acids. (f.) Dibasic acid mixtures by nitric acid oxidations. Depending upon conditions, both saturated and unsaturated fatty acids are oxidized to a heterogeneous mixture of mono- and dibasic acids by oxidation with nitric acid.     

Development of PU Coatings from Neem Oil Based Alkyds Prepared by the Monoglyceride Route

This work deals with the preparation of alkyd resins from neem oil and their utilization in preparation of polyurethane coatings. Alkyd resins were synthesized by reaction of neem oil monoglycerides with four different divalent acids like phthalic anhydride, maleic anhydride, itaconic acid, and dimer fatty acid. The alkyds formation was studied by determining the acid number of the reaction mixture at regular intervals of time and the extents of the polyesterification reactions were calculated during the formation of alkyds. The structures of synthesized alkyds were confirmed by FT‐IR and ¹H‐NMR spectroscopic analysis and also by end group analysis such as hydroxyl and acid values. The synthesized alkyds were reacted with TDI to prepare PU coatings and their performance was compared with PU coatings prepared from a commercial alkyd.     

DC-Trennung von Ricinusölfettsäure-Partialglyceriden

Thin-Layer Chromatographic Separation of Partial Glycerides of Castor Oil Fatty Acids Partial glycerides of castor oil fatty acids and hydrogenated castor oil fatty acids were prepared by esterification or glycerolysis and fractionated, together with commercial products, by TLC (especially by two-dimensional technique) on silicagel 60 precoated plates. By comparison of the two-dimensional chromatograms of the partial esters of castor oil fatty acids with synthetic standards, such as partial glycerides of ricinoleic, di- and tri-ricinoleic acids, estolides of castor oil fatty acids esterified to partial glycerides, and partial esters of castor oil fatty acids with 1,3-propanediol, the substances that could be identified were partial glycerides of ricinoleic, diricinoleic and triricinoleic and tetraricinoleic acids as well as partial glycerides, which contained, in addition to ricinoleic, diricinoleic and triricinoleic acids, fatty acids without hydroxyl groups as terminal estolide chain. The TLC enables an insight into the complex character of the glyceride composition of partial glycerides of castor oil fatty acids.     

Polymeric additives for pour point depression of residual fuel oils

Esters of styrene-maleic anhydride copolymers were synthesised by reacting styrene with maleic anhydride and esterifying the product with fatty alcohols. The resulting copolymers were purified and tested as pour point depressants for residual fuel oils. Comparative evaluation of these esters of styrene-maleic anhydride copolymers with some commercial additives showed their good activity.     

Characteristic properties of cutting fluid additives derived from the adducts of diamines and acid chlorides

A number of N,N′-diacylalkyldiamines were prepared from the reaction of acid chlorides with 1,8-diaminooctane and 1,12-diaminododecane and screened for anti-rust properties and antimicrobial activity in spent coolants of water-based cutting fluids. Aqueous solutions of N,N′-dihexanoyl-1,8-diaminooctane and N,N′-isobutyroyl-1,12-diaminododecane showed good anti-rust properties for water-based cutting fluids. Aqueous emulsions of N,N′-dibutyroyl-, dipentanoyl-, dihexanoyl- and dioctanoyl-1,12-diaminododecane showed good lubricities and antimicrobial activity for water-based cutting fluids.     

Trifunctional Acids Derived from Dehydrated Hardened Castor Oil

Dehydration and splitting of hydrogenated castor oil produces a mixture of fatty acids containing about 80% of the iso-oleic acids having the double bond in 11 and 12 positions in approximately equal proportions (as demonstrated by periodate/permanganate scission) and largely in the trans configuration. This technical iso-oleic acid reacts as expected with maleic anhydride to produce a mixture of isomeric iso-oleyl succinic anhydrides. When the oleate is reacted as the methyl ester the crude product can be distilled to produce methyl iso-oleyl succinic anhydride (M. O. S. A.) free from polymeric material. The yields of product under different conditions of time, temperature and ratio of maleic anhydride to fatty esters have been studied.     

Stereospecific hydration of unsaturated fatty acids by bacteria

Three new 10-hydroxy fatty acids, all optically active, have been prepared by the anaerobic microbiological hydration of acis-9 double bond. Substrates that formed these new hydroxy fatty acids are linoleic, linolenic, and ricinoleic acids. The hydroxyl group has the D configuration and the methyl esters are levorotatory. Infrared, mass spectral, specific rotation and ultraviolet data on these compounds were determined. There was no migration of the unreated double bonds at C₁₂ and C₁₅ in linoleic or linolenic acids. The presence of a double bond in the 10-hydroxy fatty acids significantly increased the optical rotation of the methyl esters. The hydratase enzyme showed unusual specificity among Δ⁹ unsaturated acids. While it hydrates methylene interrupted and hydroxy unsaturated acids, it failed to hydrate either 9-decenoic, 12,13-epoxy- or 12-keto-cis-9-octadecenoic acids or sterculic acid. Presented at the AOCS Meeting, San Francisco, April 1969. No. Marketing and Nutrition Res. Div., ARS, USDA.     

Preparation and characterization of a number of amine salts of long-chain fatty acids

Summary Eighty-eight amine salts of long-chain fatty acids have been prepared, purified by solvent crystallization, and characterized. Forty-five of these were salts of palmitic acid. The rest included salts of capric, lauric, myristic, stearic, oleic, elaidic, and 12-hydroxystearic acids. A variety of aliphatic, aromatic, and heterocyclic amines, including primary, secondary, and tertiary amines, were investigated. The majority of these gave 1∶1 acid-amine compounds on solvent recrystallization of an equimolar mixture of acid and amine. Some of the amines gave no crystallizable salt, and with others the pure salt could not be obtained by this procedure. Under the same conditions the symmetrical alkyl, substituted alkyl, and aralkyl secondary amines investigated gave crystallizable compounds containg two molecules of fatty acid to one of amine. Molecular compounds of 2-aminopyridine with four molecules of saturated fatty acid were formed by recrystallization starting with a 1 to 4 amine-acid mixture. Surface-tension measurements were made for aqueous solutions of a few of the amine salts. One of the laboratories of the Southern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.